IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Entomopathogenic nematodes application for controlling Lobesia botrana in grapevine and their impact on grapevine quality 

Entomopathogenic nematodes (EPN) are well-known biological control agents combined with specific adjuvants that now allow their use against aerial pests. Lobesia botrana (Lepidoptera: Tortricidae) is one of the major harmful pests detected in worldwide vineyards. Previous studies demonstrated that the EPNs Steinernema feltiae and S. carpocapsae could control L. botrana. The hypothesis was that the best combination of EPN-adjuvant/timing (season/temperatures) will support the use of EPN in the vineyard against L. botrana with no impact on the grape performance.

SHIRAZ FLAVONOID EXTRACTABILITY IMPACTED BY HIGH AND EXTREME HIGH TEMPERATURES

Climate change is leading to an increase in average temperature and in the severity and occurrence of heatwaves, and is already disrupting grapevine phenology. In Australia, with the evolution of the weather of grape growing regions that are already warm and hot, berry composition including flavonoids, for which biosynthesis depends on bunch microclimate, are expected to be impacted [1]. These compounds, such as anthocyanins and tannins, contribute substantially to grape and wine quality. The goal of this research was to determine how flavonoid extraction is impacted when bunches are exposed to high (>35 °C) and extreme high (>45 °C) temperatures during berry development and maturity.

Assessing reserve nitrogen at dormancy for predicting spring nitrogen status in Chardonnay grapevines

Nitrogen (N) supply strongly influences vine productivity and berry composition, matching availability and uptake requirements of vines during the growing season is essential to optimize vine nutrition. The nutritional status of grapevines is commonly assessed by the determination of petiole nutrient concentrations at flowering. The reserve N could also be an earlier indicator for grapevine N status, this work aimed to assess how the petiole levels relate to these perennial N reserves.

NOVEL BENZENETHIOLS WITH PHENOLS CAUSE ASHY, SMOKE FLAVOR PERCEPTION IN RED WINES

Smoke impacts on wines are becoming a worldwide problem; the size and severity of wildfires increasing due to influences from changing climates.¹ For over a century, wines have been known to have a unique issue of absorbing chemical compounds derived from wildfire smoke wherein the flavor of the subsequent wine becomes ashy, rubbery, campfire-like, and smoky.² The economic impacts of a smoke-impacted wine can last for years depending on the grape varietal, costing Oregon and Washington states in the United States over a billion dollars from the 2020 wildfires, as an example.³ While years of research have indicated elevated concentrations of smoke-related compounds, such as guaiacol and syringol, in wines after smoke events, unfortunately, replicating the sensory experience using smoke-associated phenols has not had much success.⁴

Hormone metabolism regulates fruit maturation in a slow ripening grape genotype

Context and purpose of the study. Rising temperatures and prolonged heat accelerate berry sugar accumulation in advance of the accumulation of compounds responsible for aroma, colour and mouthfeel.